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Concise and practical route to tri- and tetra-hydroxy seven-membered iminocyclitols as glycosidase inhibitors from d-(+)-glucurono-γ-lactone
Ist Teil von
Tetrahedron, 2010-10, Vol.66 (44), p.8522-8526
Ort / Verlag
Kidlington: Elsevier Ltd
Erscheinungsjahr
2010
Link zum Volltext
Quelle
Elsevier ScienceDirect Journals Complete
Beschreibungen/Notizen
An efficient and short total synthesis of tetrahydroxy-
1c and trihydroxy-azepane
1d is reported in 72% and 57% overall yields, respectively, from
d-(+)-glucurono-γ-lactone. Thus,
d-glucuronolactone
2 on acetonide protection, DIBAL-H reduction and one-pot intermolecular reductive amination followed by –
NCbz protection afforded 6-(
N-benzyl-
N-benzyloxycarbonyl) amino-6-deoxy-1,2-
O-isopropylidene-α-
d-
gluco-1,4-furanose
5a. 1,2-Acetonide hydrolysis in
5a and Pd-mediated intramolecular reductive aminocyclization afforded tetrahydroxyazepane
1c. An analogous pathway with 5-deoxy-1,2-
O-isopropylidene-α-
d-glucurono-6,3-lactone
3b gave trihydroxy-azepane
1d. Glycosidase inhibitory activity of
1c/
1d was studied and
1d was found to be potent inhibitor of α-mannosidase and β-galactosidase.
A short and highly efficient synthesis of two iminocyclitols
1c and
1d, from cheap starting material
d-(+)-glucuronolactone using only two protecting groups (acetonide, Cbz) and their glycosidase inhibitory activity study is reported.
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